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Tandem Nucleophilic Addition/Diels–Alder Reaction of N ‐Butadienyl N , O ‐Ketene Silyl Acetals with C 60 : Stereoselective Formation of Bicyclic Octahydroquinolino‐1,2,3,4‐Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions
Author(s) -
Rubin Yves,
Ganapathi Padma S.,
Franz Andreas,
An YiZhong,
Qian Wenyuan,
Neier Reinhard
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19991105)5:11<3162::aid-chem3162>3.0.co;2-h
Subject(s) - ketene , bicyclic molecule , stereoselectivity , silylation , chemistry , tandem , nucleophile , nucleophilic addition , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , composite material
As a preliminary step in our quest for 1,2,3,4,5,6‐hexahydro derivatives of C 60 —which should ring‐open spontaneously in a retro [2+2+2] fashion to form a large orifice permitting the introduction of metals into the fullerene cage—we have created a family of highly congested 1,2,3,4‐tetrahydrobuckminsterfullerene derivatives 1 .